hexa-2,4-diene-2,3,4,5-tetrayltetrabenzene | 16914-14-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: hexa-2,4-diene-2,3,4,5-tetrayltetrabenzene
• 英文别名: 2.3.4.5-Tetraphenyl-hexadien-(2.4)；2,4,5-triphenylhexa-2,4-dien-3-ylbenzene
• CAS: 16914-14-0
• 化学式: C₃₀H₂₆
• 分子量: 386.536
• InChiKey: HRTOUKIGMXQSIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N'-(1,2-diphenylpropylidene)-4-methylbenzenesulfonohydrazide 在 bis-triphenylphosphine-palladium(II) chloride 、 亚磷酸二乙酯 、 对苯醌 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以68%的产率得到hexa-2,4-diene-2,3,4,5-tetrayltetrabenzene
  参考文献：
  名称：

  Pd-Catalyzed Cross-Coupling Reactions of Hydrazones: Regioselective Synthesis of Highly Branched Dienes

  摘要：

  The regioselective formation of highly branched dienes is a challenging task. Design and exploration of alternative working models to achieve such a regioselectivity to accomplish highly branched dienes is considered to be a historical advancement of Heck reaction to construct branched dienes. On the basis of the utility of carbene transfer reactions, in the reaction of hydrazones with Pd(II) under oxidative conditions, we envisioned obtaining a Pd-bis-carbene complex with α-hydrogens, which can lead to branched dienes. Herein, we report a novel Pd-catalyzed selective coupling reaction of hydrazones in the presence of t-BuOLi and benzoquinone to form the corresponding branched dienes. The utility of the Pd catalyst for the cross-coupling reactions for synthesizing branched conjugated dienes is rare. The reaction is very versatile and compatible with a variety of functional groups and is useful in synthesizing heterocyclic molecules. We anticipate that this Pd-catalyzed cross-coupling reaction will open new avenues for synthesizing useful compounds.

  DOI：

  10.1021/jo402153t